(R)-2-{(2R,3R,4R,5R)-5-Benzyloxy-4-icosanoylamino-2-[(R)-2-icosanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid

Base Information

Chemical Name:(R)-2-{(2R,3R,4R,5R)-5-Benzyloxy-4-icosanoylamino-2-[(R)-2-icosanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid
CAS No.:82816-67-9
Molecular Formula:C₆₁H₁₀₈N₂O₉
Molecular Weight:1013.54
Hs Code.:

(R)-2-{(2R,3R,4R,5R)-5-Benzyloxy-4-icosanoylamino-2-[(R)-2-icosanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid

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Chemical Property of (R)-2-{(2R,3R,4R,5R)-5-Benzyloxy-4-icosanoylamino-2-[(R)-2-icosanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid

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Technology Process of (R)-2-{(2R,3R,4R,5R)-5-Benzyloxy-4-icosanoylamino-2-[(R)-2-icosanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid

There total 9 articles about (R)-2-{(2R,3R,4R,5R)-5-Benzyloxy-4-icosanoylamino-2-[(R)-2-icosanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 81148-68-7
benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside

: 82816-67-9
(R)-2-{(2R,3R,4R,5R)-5-Benzyloxy-4-icosanoylamino-2-[(R)-2-icosanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / pyridine / 5 h / -10 °C

2: 96 percent / 1.) p-toluenesulfonic acid monohydrate; 2.) Amberlite IR-45 (OH^-) ion-exchange resin / dioxane / 3 h / Ambient temperature

3: 87 percent / sodium azide / dimethylformamide / 15 h / 80 °C / Heating

4: Raney Ni (W-1) / ethanol / 1.5 h / Ambient temperature

5: dioxane / 5 h / Ambient temperature

6: hydrogen / 10 percent Pd-C / ethanol / 1 h / Ambient temperature

7: dioxane / 8 h / Ambient temperature

8: 1.) 0.1 M potassium hydroxide; 2.) Amberlite IR-120B (H⁺) resin / dioxane / 1 h / Ambient temperature

With pyridine; potassium hydroxide; sodium azide; Amberlite IR-120B (H⁺) resin; Amberlite IR-45 (OH^-) ion-exchange resin; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; Raney Ni (W-1); In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)80687-4

Reference yield:

: 81161-21-9
(R)-2-{(2R,3R,4R,5R)-2-[(R)-2-Amino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-5-benzyloxy-4-benzyloxycarbonylamino-tetrahydro-furan-3-yloxy}-propionic acid methyl ester

: 82816-67-9
(R)-2-{(2R,3R,4R,5R)-5-Benzyloxy-4-icosanoylamino-2-[(R)-2-icosanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid

Guidance literature:: Multi-step reaction with 4 steps

1: dioxane / 5 h / Ambient temperature

2: hydrogen / 10 percent Pd-C / ethanol / 1 h / Ambient temperature

3: dioxane / 8 h / Ambient temperature

4: 1.) 0.1 M potassium hydroxide; 2.) Amberlite IR-120B (H⁺) resin / dioxane / 1 h / Ambient temperature

With potassium hydroxide; Amberlite IR-120B (H⁺) resin; hydrogen; palladium on activated charcoal; In 1,4-dioxane; ethanol;
DOI:10.1016/S0008-6215(00)80687-4

Reference yield:

: 81148-76-7
benzyl 2-(benzyloxycarbonylamino)-2-deoxy-6-O-mesyl-3-O--β-D-glucofuranoside

: 82816-67-9
(R)-2-{(2R,3R,4R,5R)-5-Benzyloxy-4-icosanoylamino-2-[(R)-2-icosanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / 1.) p-toluenesulfonic acid monohydrate; 2.) Amberlite IR-45 (OH^-) ion-exchange resin / dioxane / 3 h / Ambient temperature

2: 87 percent / sodium azide / dimethylformamide / 15 h / 80 °C / Heating

3: Raney Ni (W-1) / ethanol / 1.5 h / Ambient temperature

4: dioxane / 5 h / Ambient temperature

5: hydrogen / 10 percent Pd-C / ethanol / 1 h / Ambient temperature

6: dioxane / 8 h / Ambient temperature

7: 1.) 0.1 M potassium hydroxide; 2.) Amberlite IR-120B (H⁺) resin / dioxane / 1 h / Ambient temperature

With potassium hydroxide; sodium azide; Amberlite IR-120B (H⁺) resin; Amberlite IR-45 (OH^-) ion-exchange resin; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; Raney Ni (W-1); In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)80687-4